In the early days of CCAW, I often found myself distracted. I call it founder squirrel syndrome. It’s common—maybe, I’d argue, the norm. I poured tons of my energy into things that wouldn’t get me closer to my next milestone. I distinctly remember spending a great deal of time improving our order fulfillment process—which wouldn’t keep the lights on. We needed to get to a certain revenue threshold to be at the cash flow break-even point. We needed paying customers. I should have focused on landing new customers, not making things pleasant for our few existing ones. Over time I learned, albeit in a painful way, and it all worked out.

Early founders have so much coming at them that it’s hard to focus on, or sometimes even identify, what matters most. The early startup days are chaotic. Everything is all over the place. Nothing goes as planned. Constantly calling audibles. Reacting to new information. In the midst of all this, tending to what matters most can be the difference between success and failure because resources are precious. There are only so many hours in the day and dollars in the bank. Use them wisely. Less critical things can be dealt with later.

This is one of the hardest concepts for early founders to grasp and also one of the most impactful. If you’ve founded a company or are considering it, learn to set a few milestones and focus your efforts on activities that help you reach them. If you don’t know how to go about doing this, reach out. Ask for help. Learning this skill early can be a game changer!

Finding a cofounder is difficult, especially for nontechnical solo founders building tech companies. The pandemic has made the task even harder. Hearing so many founders struggle with this has kept it top of mind for me. Here are a few resources I’ve recently heard founders mention when they describe how they found technical cofounders:

• AngelList – A community focused specifically on startups. There’s area place to post jobs. The site’s focus on startups should help in reaching people who want to work with an early-stage company.
• GitHub – A development platform that helps technical teams with collaboration, version control, and a host of other things. A community forum mostly counts developers as members.
• Slack – This is specific to Atlanta (kinda). There’s a workspace for the Atlanta tech community called "tech404." Many developers are in the workspace, and there’s a channel specifically for jobs and another for gigs. I’ve encountered people who are part of the workspace but don’t live in Atlanta. I assume these kinds of workspaces exist in other major cities or regions too.
• Network blast – I’ve heard of founders sending out descriptions of the type of experience they were looking for via emails or texts. Potential cofounders were often suggested by people the founder would least expect to be helpful. You never know who someone else knows.
• Virtual events – This is harder, but I’ve heard of founders attending startup or technical events that offer virtual networking. Events that use platforms like Hopin can give you the chance to network one-on-one with people you might not otherwise meet.

I’m always surprised by the creative ways people connect with cofounders. I thought it might be helpful to share some of these. I can’t say if these will work for everyone, but I do know one thing for sure. If you don’t take action, you won’t find a cofounder. Be action-oriented and creative and you just might end up finding a technical cofounder who complements you.

This problem won’t go away, so I’ll update and share this list periodically. I hope it’s helpful.

At the end of each year, I think about what’s important to me that I want to focus on during the next year. I usually come up with a short list of three or four things—some personal and some professional. For each one, I identify the metric that will help me gauge how I’m doing and what success looks like (i.e., a target value for the metric). For example, I wanted to be more intentional about personal relationships in 2020, so I tracked how many activities I initiated with friends and family each month. My goal was five.

I don’t do this in isolation. I do it with a group of entrepreneurs so we can hold each other accountable. We track our goals in a central place and discuss our progress every month. If someone isn’t moving in the right direction in a particular area, we dig into the reasons for that.

When I set my targets in December, I’m nowhere close to achieving them. And I usually have no idea how I’ll reach them. I just know they represent what’s important to me and that I want to improve in that area. I know it won’t be easy, but I’m committed to figuring out how to move the needle through the year.

Today I reviewed my October metrics with my group and looked back over 2020. I had set a few stretch targets that I wasn’t confident about achieving. I was pleased to realize that I’ve achieved each stretch goal, even those that seemed unattainable. I thought about why and came up with a few reasons:

• Cadence – The regular rhythm of revisiting and discussing goals every month keeps them top of mind.
• Accountability – I don’t want to be the slacker in my peer group. Especially concerning goals I set for myself! I push harder so I don’t embarrass myself.
• Motivation – Taking time to pinpoint what’s important is key for me. When I identify the right things, it feels natural to work at improving them.
• Short list – I measure four things, max. I don’t think I’d be able to focus on more than that.
• Balance – Including personal and professional things helps me feel like the progress I’m making is balanced. It’s too easy to do well in one area to the detriment of the other.

It’s rewarding to monitor my progress throughout the year and the positive effects it’s had. I’m looking forward to settling on what’s important to me for 2021 during the holidays.

What about you? What do you want to work on in 2021? How will you measure your progress?

In the early days of a startup, the founders are the glue. The vision for the company is in their head. They understand better than anyone how all the pieces fit together. With minimal resources, they’re usually involved in all aspects of the business because the team is so small, junior, or part-time (e.g., composed of contractors or interns). Founders are holding it all together and driving it forward. Founders are the duct tape and the bubble gum. If they aren’t around, things go sideways or screech to a halt. Fear becomes ingrained in their head: if they don’t do it, it won’t get done or it won’t get done right.

This is normal and can be beneficial in the early days. It can be the key to finding product–market fit. Being involved in everything allows the founder to get feedback directly from customers and adjust the entire business quickly. They can continually do this until product–market fit is achieved. Achieving product–market fit before the company runs out of runway is many times harder if the founder isn’t around.

Once product–market fit is achieved, though, this quickly starts to work against the company. Once you’ve fine-tuned your solution and your customers see its value and readily pay for it, it’s time to scale. As you scale, or try to, everything gets bigger. The team, number of customers, and initiatives all grow. With this complexity, the small startup that once relied on its founders is now it’s own living thing. It becomes impossible for the founders to have their hands in everything. There’s too much going on for it to all flow through founders. There aren’t enough hours in the day. If founders insist on continuing to be the glue, they become a bottleneck. Decision-making and growth slow drastically. Team members may become frustrated and leave.

Lots of founders don’t realize their insistence on being the glue is thwarting growth. It happened to me at CCAW and to many other founders I know. Once a founder figures this out, they should adjust quickly. I did this at CCAW, putting my trust in direct reports to make the right decisions to achieve our metrics. I was relieved. It was hard to not know everything, but I soon realized that it freed me up to think more strategically and see the business through a different lens. I was no longer in the weeds. I wasn’t even worried about the trees. I was looking at the forest!

If you’re a new (or newish) founder, you should understand that being the glue for your company is important. But when the company has entered its next phase, you need to put the right people, systems, and processes in place to allow the company to grow. It’s OK if you don’t know everything, and you’re not involved in everything. It’s means you’ve done a good job and your baby is becoming an adult!

A few months back, I shared that CCAW’s technology became the secret sauce that allowed us to scale quickly. At a very high level, our technology focused on workflow management. We built it for internal use over many years. It was customized to our needs, so we never considered offering it for sale.

Over the last few weeks, I’ve had a few conversations with entrepreneurs who also built workflow technology internally. They now believe their technology has broader applications, and they’re building platforms to help other companies standardize and automate aspects of their businesses. I think they’re on to something and will build large businesses themselves.

Workflow-management technology is a great foundation upon which to build a tech company. The concept can be applied to numerous aspects of a business. And many things are still done manually or inefficiently, so the opportunity for improvement with technology is significant. A number of technology companies have built wildly successful workflow-management technology businesses that serve as blueprints for early entrepreneurs. (Click on the link to my previous article, above, for specific companies.)

I’m a nontechnical founder, but with my team I was able to build a large company underpinned by technology. And I’m not the only one. Nontechnical founders who want to build a great technology company as their second act can do well basing it on workflow-management tech. If they’ve lived the problem in their first company, they’ve amassed invaluable knowledge. With it, they have a ready-made founder–market fit, and they’re perfectly positioned to solve the problem better than others. (If you’ve been reading my posts for a while, you may recall that I’ve talked about this—a founder’s unfair advantage—before.)

This organic knowledge also helps these founders clearly articulate a compelling vision that they’re genuinely passionate about. They’re usually looking to create a world without XYZ problem in it so other people don’t have to experience the pain they did. Such a vision is a great recruiting tool, especially for attracting a technical co‑founder. Their remembered pain can also help these founders empathize with what their potential customers are experiencing, which can help drive the vision for the product.

Today, Outlander Labs hosted its first Outlandish Speaking Series. It’s our way of giving Southeast founders the opportunity to hear from high-quality speakers they otherwise might not. At today’s event, (click "View Details"), Eric Feng, Facebook’s head of commerce incubation, shared insights about the importance of timing in start-up fundraising. Eric was a Hulu founder and general partner at Kleiner Perkins; he’s seen start-up life from a variety of angles.

Eric’s insights were fantastic. Here are some of my core takeaways:

• Missionaries vs. mercenaries – Missionaries are better entrepreneurs than mercenaries because they’re driven by passion. This video explains it well.
• Runway and risk – Fund-raising adds runway to remove risk and grow value. As you raise later rounds of capital from investors, you should be removing risk with each round. For example, you shouldn’t be raising your series B funding without building a product and understanding whether prospective customers want what you’re building (i.e., whether there’s a product–market fit).
• Seed stage – Early investors (pre-seed and seed) understand that pretty much everything is a risk because they’re investing so early in the company’s life cycle. You may have only two people (not a full team), the product might barely work (implementation risk), and you may not have a clear idea whether people will pay for your product (so you don’t have a product–market fit yet).
• Opportunity window – Understanding whether something is an opportunity or a window of opportunity is important. If a window will close on the opportunity, consider grabbing it as soon as you can. Later may be too late. All opportunities aren’t equal, so don’t wait forever if you see a good one.

Today’s session was great and Eric was an amazing speaker. He has a wealth of knowledge that he readily shared with the audience. I’m looking forward to next month’s Outlandish Speaking Series. If you’re interested in attending or seeing other Outlander events, feel free to check them out here or here.

Today I participated in an idea session with my Outlander Labs teammates. No agenda, just a topic and a conversation about ideas. It was a topic that I’m not knowledgeable about, so my goal was to listen and learn. And boy, did I! The team’s collective knowledge was vast and we ended up with great ideas. Today was an opportunity for me to fill a knowledge gap, and it highlighted something else for me too.

As I listened, I noticed a pattern. Idea compounding. Sounds weird, so let me explain. Our team is composed of highly intelligent people who, individually, have great ideas and unique perspectives. As one person shared a thought, you could see the wheels turning in everyone else’s head. Then someone else shared an idea inspired by the previous one. This went on for an hour and resulted in more great ideas than we can possibly execute. A high-class problem for sure.

Our idea-generating exercise was highly effective because we approached the topic as a team. Had we assigned it to one person, I have no doubt that their ideas would have been really good. But approaching it as a team resulted in ideas that are great (or so we think).

I wish I had had the benefit of idea compounding in my early days at CCAW. I chose the solo founder path, and it was difficult. I was forced to come up with all the ideas, which were far from great. Years later I hired high-level thinkers and our idea compounding led to some of CCAW’s greatest breakthroughs. We overcame enormous hurdles and made tons of traction in a relatively short time.

Idea compounding is one of the many benefits of working with a team. And great ideas can be the difference between success and failure for early-stage companies. For any founder wondering why you should consider recruiting a co-founder: idea compounding is one of the many reasons you shouldn’t go it alone!

I’m often asked why I didn’t raise capital from investors at CCAW, instead choosing to bootstrap. I think people expect to hear some strategic thought-out reason. The truth is much simpler. I didn’t know any better. That may sound ridiculous. Let me clarify a bit.

Not raising capital forced me to be capital-efficient, but it also resulted in challenges. Most of them I didn’t recognize until much later. We had customer revenue from day one, so I viewed us as different from companies that burn cash for months while they build a product. Customer cash flows were fine in the beginning, but as I started to think more strategically it wasn’t enough. We had enough money to pay salaries and other operating expenses, but sometimes we didn’t have enough left to invest in strategic projects. And if we did, we didn’t have enough for the entire project.

I found myself in a situation where I couldn’t afford the appropriate resources for the entire time it would take for these projects to pay off. This resulted in a start-and-stop rhythm. We’d start, run out of money, and stop until we got enough in the bank to start again. This extended projects unnecessarily and frustrated the team. Really big projects can require people who work on nothing else. With some of them, it takes a year or two before you see an ROI. That means paying salaries for two years without a contribution to revenue or profitability. We couldn’t afford to carry salaries on the books that long if they didn’t result in revenue. Our large projects were understaffed at times or simply never happened. Strategic projects are what move most companies forward. We never had enough runway to execute properly on our strategic projects. We had too many conflicting draws on our limited capital.

With the benefit of hindsight, I’d do lots of things differently. Mainly, I’d think hard about the resources needed to implement my vision. That would take time, but I’d identify the first major milestones. The milestones would be early indicators of success. For CCAW, that would’ve been early signs of increasing revenue. I’d determine what people and resources were needed and what the time frame was. I’d put all that into a simple budget. That budget, along with my vision, would have been great tools for soliciting investor capital. Had I gotten an investor, it might have given me the breathing room we needed to start working toward my vision. Notice I didn’t say it would’ve been enough capital to make the vision reality—just enough to show others that my team had what it took to make progress. If we were successful, I’m sure additional capital would have been easy to come by.

Hindsight is 20/20, and I wouldn’t change anything about my journey. The situation I’ve described isn’t unique to me. I regularly speak with entrepreneurs in similar situations. They just don’t have enough breathing room to begin executing.

If you’re in that situation, considering identifying short-term milestones that will show you’re headed in the right direction. Couple them with a timeline and budget and you’ll have a powerful tool that will help others understand your vision. Asking for a small amount of capital (just enough to allow you to make some progress) de-risks you as an investment. You will still hear “no” from lots of investors, but you’re more likely to find one willing to give you a shot. There’s a lot to be said for breathing room!

I met with an entrepreneur who’s addressing a unique problem in the automotive space. He’s done lots of customer discovery and is looking to build an early version of his MVP. And he wants to build a marketplace and asked for my insights. We didn’t build a marketplace at CCAW, but we overcame challenges similar to those encountered by marketplaces. After a decade of hitting our heads against a wall, this is what we learned:

• Customer acquisition – Don’t outsource customer acquisition or use third-party software long-term. Third-party platforms (Shopify, Magento, etc.) are cost-effective to begin with, but they will eventually hinder you. These platforms aren’t built with your specific problem in mind. They have to appeal to many, so they must be somewhat generic. This will prevent your solution from being great. It will only be somewhat good. You try to customize the platform to overcome this. The more you spend to customize it, the harder it is to transition away from it. Such platforms will never be as good as building your own technology from scratch. All successful marketplaces (Airbnb, eBay, Etsy) built technology to nail solving the problems they saw.
• Product catalog – This is hard to address, but it’s critical. Don’t underestimate it. Understand the products you’re selling and build technology to manage the catalog properly. Don’t outsource the catalog or use third-party software long-term to manage it. We had about thirty thousand products in our catalog at CCAW. Taking the time to build technology to store that catalog gave us a huge competitive advantage.
• Pricing – This is one of the most important things in marketplaces. The right products with the wrong prices won’t sell. If pricing is calculated (i.e., not provided by the sellers), invest in developing your own technology long-term. (Are you seeing a pattern here?) We built a dynamic pricing engine at CCAW that became part of our secret sauce. It was frustrating and took a year to perfect, but once it was finished it was a thing of beauty and a big competitive advantage.
• Supply – This advice is more specific to the automotive industry, but I’ll share it anyway. You don’t want to go too big or small when you’re finding your first suppliers or sellers. Find companies large enough to have adequate systems and processes in place so they will be reliable and provide data in a consistent automated manner. Medium-sized players usually have these things, plus they’ll value the relationship. Big players typically won’t see the value in working with early companies; it’s more of a nuisance to them. Smaller players will be eager to work with you, but their lack of systems and processes will be an issue. Starting with one or two medium players is usually enough to test. Remember, your goal is to learn what you don’t know. We started out with one supplier at CCAW. Once we finished learning, we courted larger companies that were by that time eager to work with us because we had our act together and they’d heard good things about us.
• Supply side operations – Don’t worry about things like shipping, returns, and customer service at the MVP stage. You can manually handle this stuff with a patchwork of tools like Excel, Gmail, etc. They’re important, but not as important as getting the demand side (customer acquisition) right. First things first. Focus on acquiring customers effectively before you invest in supply side operations. If you can’t get any customers, you won’t need better systems on the supply side.

My biggest learning was the importance of focusing on the demand side when you’re building a marketplace MVP. Yes, you absolutely need supply, but you don’t need to have a world-class supply side operation or a ton of supply sources. Understand the customer’s pain points and address them. Doing so will help you accumulate customers and keep them coming back. If you nail this, you’ll have more customers than you know what to do with and then you can fix everything else!

I used to enjoy reading box office rankings every week. Movies were ranked by total gross sales that were reported by theatres nationwide to a central organization, which published the data. It was my way of staying in tune with popular culture. It also helped me understand just how massive the movie business is. Yes, I know this is super nerdy, but hey, it worked for me. I haven’t followed these in a few years and hadn’t thought much about why until yesterday.

A sharp founder connected the dots for me. Box office sales are no longer an accurate reflection of consumer movie-viewing habits. This has been the case for the last few years, and the pandemic accelerated this trend and at the same time completely halted the collection of this data. Content creation has historically been dominated by large studios, with movies being distributed through theatres. Box office receipts helped creators understand how their content performed with audiences and estimate its future value. Equally high-quality content is now distributed (and sometimes created) by platforms like Netflix, Hulu, and Amazon Prime Video. As I understand it, these platforms don’t share their viewership data. So how do creators know how their content is performing on a platform or across multiple platforms? They don’t. Without viewership data, it’s difficult for creators to understand the value of their content. This is a big problem that creators are trying to solve. There are companies actively working on it, but I don’t believe anyone has solved it in a way that all stakeholders will readily adopt.

Distribution varies by industry, but at a high level it’s how a product or service reaches customers. Distribution methods have been evolving over the last decade, with the pace of change constantly accelerating. Especially now, with COVID-19 looming over everything. After entrepreneurs achieve product–market fit (i.e., customers readily pay for their solution), they should be thinking about how their product or service will reach their customers.